Enzymic resolution and binding to rat brain membranes of the glutamic acid agonist .alpha.-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid

Journal of Medicinal Chemistry
1983.0

Abstract

The enantiomers of the glutamic acid central nervous system receptor agonist alpha-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) were prepared via kinetic resolution of the racemic N-acetylated 3-methoxy derivative by reusable, immobilized aminoacylase. L-AMPA was more effective (IC50 = 0.6 microM) than D-AMPA (IC50 = 4.8 microM) in displacing racemic [3H]AMPA from binding sites on rat brain synaptic membranes in agreement with their relative in vivo excitatory potencies.

Knowledge Graph

Similar Paper

Enzymic resolution and binding to rat brain membranes of the glutamic acid agonist .alpha.-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid
Journal of Medicinal Chemistry 1983.0
Excitatory amino acid agonists. Enzymic resolution, x-ray structure, and enantioselective activities of (R)- and (S)-bromohomoibotenic acid
Journal of Medicinal Chemistry 1989.0
N-Methyl-<scp>d</scp>-aspartic Acid Receptor Agonists:  Resolution, Absolute Stereochemistry, and Pharmacology of the Enantiomers of 2-Amino-2-(3-hydroxy-5-methyl-4-isoxazolyl)acetic Acid
Journal of Medicinal Chemistry 1996.0
Resolution, Absolute Stereochemistry, and Pharmacology of the S-(+)- and R-(-)-Isomers of the Apparent Partial AMPA Receptor Agonist (R,S)-2-Amino-3-(3-hydroxy-5-phenylisoxazol-4-yl)propionic Acid [(R,S)-APPA]
Journal of Medicinal Chemistry 1994.0
Ibotenic Acid Analogues. Synthesis, Molecular Flexibility, and in Vitro Activity of Agonists and Antagonists at Central Glutamic Acid Receptors
Journal of Medicinal Chemistry 1985.0
Structure−Activity Studies for α-Amino-3-hydroxy-5-methyl-4-isoxazolepropanoic Acid Receptors:  Acidic Hydroxyphenylalanines
Journal of Medicinal Chemistry 1997.0
Excitatory Amino Acid Receptor Ligands:  Resolution, Absolute Stereochemistry, and Enantiopharmacology of 2-Amino-3-(4-butyl-3-hydroxyisoxazol-5-yl)propionic Acid
Journal of Medicinal Chemistry 1998.0
Heterocyclic excitatory amino acids. Synthesis and biological activity of novel analogs of AMPA
Journal of Medicinal Chemistry 1992.0
AMPA Receptor Agonists:  Synthesis, Protolytic Properties, and Pharmacology of 3-Isothiazolol Bioisosteres of Glutamic Acid
Journal of Medicinal Chemistry 1997.0
Excitatory amino acid receptor atagonists: synthesis and pharmacology of 3-(carboxymethoxy)isoxazoles derived from AMPA
Bioorganic &amp; Medicinal Chemistry Letters 1993.0